Synthesis of Lipophilic Esters of Tyrosol, Homovanillyl Alcohol and Hydroxytyrosol
Low-molecular weight phenols such as tyrosol, homovanillyl alcohol and hydroxytyrosol are valuable compounds that exhibit a high number of health-promoting effects such as antioxidant, anti-inflammatory and anticancer activity. Despite these remarkable properties, their applications such as dietary...
Main Authors: | , , , |
---|---|
Format: | Article |
Language: | English |
Published: |
MDPI AG
2019-06-01
|
Series: | Antioxidants |
Subjects: | |
Online Access: | https://www.mdpi.com/2076-3921/8/6/174 |
id |
doaj-d4f254d66c7d43cc9e29fe2903d36720 |
---|---|
record_format |
Article |
spelling |
doaj-d4f254d66c7d43cc9e29fe2903d367202020-11-25T00:42:43ZengMDPI AGAntioxidants2076-39212019-06-018617410.3390/antiox8060174antiox8060174Synthesis of Lipophilic Esters of Tyrosol, Homovanillyl Alcohol and HydroxytyrosolRoberta Bernini0Isabella Carastro1Francesca Santoni2Mariangela Clemente3Department of Agriculture and Forest Sciences (DAFNE), University of Tuscia, Via S. Camillo de Lellis, 01100 Viterbo, ItalyDepartment of Agriculture and Forest Sciences (DAFNE), University of Tuscia, Via S. Camillo de Lellis, 01100 Viterbo, ItalyDepartment of Agriculture and Forest Sciences (DAFNE), University of Tuscia, Via S. Camillo de Lellis, 01100 Viterbo, ItalyDepartment of Agriculture and Forest Sciences (DAFNE), University of Tuscia, Via S. Camillo de Lellis, 01100 Viterbo, ItalyLow-molecular weight phenols such as tyrosol, homovanillyl alcohol and hydroxytyrosol are valuable compounds that exhibit a high number of health-promoting effects such as antioxidant, anti-inflammatory and anticancer activity. Despite these remarkable properties, their applications such as dietary supplements and stabilizers of foods and cosmetics in non-aqueous media are limited for the hydrophilic character. With the aim to overcome this limitation, the paper describes a simple and low-cost procedure for the synthesis of lipophilic esters of tyrosol, homovanillyl alcohol and hydroxytyrosol. The reactions were carried out under mild and green chemistry conditions, at room temperature, solubilizing the phenolic compounds in dimethyl carbonate, an eco-friendly solvent, and adding a little excess of the appropriate C2−C18 acyl chloride. The final products were isolated in good yields. Finally, according to the “circular economy” strategy, the procedure was applied to hydroxytyrosol-enriched extracts obtained by <i>Olea europaea</i> by-products to prepare a panel of lipophilic extracts that are useful for applications where solubility in lipid media is required.https://www.mdpi.com/2076-3921/8/6/174tyrosolhomovanillyl alcoholhydroxytyrosoldimethyl carbonatelipophilic alkyl estershydroxytyrosol-enriched extracts<i>Olea europaea</i>green chemistrycircular economy |
collection |
DOAJ |
language |
English |
format |
Article |
sources |
DOAJ |
author |
Roberta Bernini Isabella Carastro Francesca Santoni Mariangela Clemente |
spellingShingle |
Roberta Bernini Isabella Carastro Francesca Santoni Mariangela Clemente Synthesis of Lipophilic Esters of Tyrosol, Homovanillyl Alcohol and Hydroxytyrosol Antioxidants tyrosol homovanillyl alcohol hydroxytyrosol dimethyl carbonate lipophilic alkyl esters hydroxytyrosol-enriched extracts <i>Olea europaea</i> green chemistry circular economy |
author_facet |
Roberta Bernini Isabella Carastro Francesca Santoni Mariangela Clemente |
author_sort |
Roberta Bernini |
title |
Synthesis of Lipophilic Esters of Tyrosol, Homovanillyl Alcohol and Hydroxytyrosol |
title_short |
Synthesis of Lipophilic Esters of Tyrosol, Homovanillyl Alcohol and Hydroxytyrosol |
title_full |
Synthesis of Lipophilic Esters of Tyrosol, Homovanillyl Alcohol and Hydroxytyrosol |
title_fullStr |
Synthesis of Lipophilic Esters of Tyrosol, Homovanillyl Alcohol and Hydroxytyrosol |
title_full_unstemmed |
Synthesis of Lipophilic Esters of Tyrosol, Homovanillyl Alcohol and Hydroxytyrosol |
title_sort |
synthesis of lipophilic esters of tyrosol, homovanillyl alcohol and hydroxytyrosol |
publisher |
MDPI AG |
series |
Antioxidants |
issn |
2076-3921 |
publishDate |
2019-06-01 |
description |
Low-molecular weight phenols such as tyrosol, homovanillyl alcohol and hydroxytyrosol are valuable compounds that exhibit a high number of health-promoting effects such as antioxidant, anti-inflammatory and anticancer activity. Despite these remarkable properties, their applications such as dietary supplements and stabilizers of foods and cosmetics in non-aqueous media are limited for the hydrophilic character. With the aim to overcome this limitation, the paper describes a simple and low-cost procedure for the synthesis of lipophilic esters of tyrosol, homovanillyl alcohol and hydroxytyrosol. The reactions were carried out under mild and green chemistry conditions, at room temperature, solubilizing the phenolic compounds in dimethyl carbonate, an eco-friendly solvent, and adding a little excess of the appropriate C2−C18 acyl chloride. The final products were isolated in good yields. Finally, according to the “circular economy” strategy, the procedure was applied to hydroxytyrosol-enriched extracts obtained by <i>Olea europaea</i> by-products to prepare a panel of lipophilic extracts that are useful for applications where solubility in lipid media is required. |
topic |
tyrosol homovanillyl alcohol hydroxytyrosol dimethyl carbonate lipophilic alkyl esters hydroxytyrosol-enriched extracts <i>Olea europaea</i> green chemistry circular economy |
url |
https://www.mdpi.com/2076-3921/8/6/174 |
work_keys_str_mv |
AT robertabernini synthesisoflipophilicestersoftyrosolhomovanillylalcoholandhydroxytyrosol AT isabellacarastro synthesisoflipophilicestersoftyrosolhomovanillylalcoholandhydroxytyrosol AT francescasantoni synthesisoflipophilicestersoftyrosolhomovanillylalcoholandhydroxytyrosol AT mariangelaclemente synthesisoflipophilicestersoftyrosolhomovanillylalcoholandhydroxytyrosol |
_version_ |
1725280651877285888 |